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    1. Local experiences/
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    5. Key West 1.5-Hour Classic Day Sailing Cruise
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    Key West 1.5-Hour Classic Day Sailing Cruise

    Sail Key West on Schooner America 2.0 with complimentary soft drinks

    4.9 stars• 592 reviews
    From$63/ personincl. taxes and fees

    Duration

    1.5 Hours

    Ideal For

    20-30 people

    Includes

    Sail, soda, juice, water

    Highlights

    Set sail on a 1.5-hour daytime cruise aboard the 105-foot Schooner America 2.0 and take in waterfront views of Downtown Key West. Enjoy onboard narration from the professional crew as you glide past local sights.

    • Spot marine wildlife like dolphins along the route
    • Learn about local history and ecology from the crew narration
    • View Downtown Key West from the water, including Mallory Square and Sunset Pier
    • Look for Fort Zachary Taylor and distant Sand Key Lighthouse from the schooner
    • Help hoist the sails or take a turn at the helm when conditions allow

    What's Included

    • 1.5-hour sailing cruise aboard Schooner America 2.0
    • Complimentary soda, juice, and water

    Things to know

    Outside alcoholic beverages are not permitted, and alcohol is available for purchase on board (credit card only). Gratuity is not included. The schooner is not wheelchair-accessible.

    Cancellation Policy

    Cancel up to 24 hours in advance for a full refund. Day-of cancellations are non-refundable/non-reschedulable. No-shows are charged in full.

    FAQs

    All passengers require a ticket, but infants under 2 sail free.

    You may bring your own food. Outside alcohol is not permitted. Alcoholic drinks can be purchased on board or during booking.

    No, America 2.0 is not wheelchair-accessible.

    Meeting details

    202R William Street, Key West FL, 33040

    Experience provided by Classic Harbor Line - Key West
    Experience provided by Classic Harbor Line - Key West

    More about Sand Key Lighthouse

    Sand Key Lighthouse rises from a small, sun-bleached shoal about seven miles southwest of Key West, marking one of the most photogenic stretches of water along the Florida Reef. Built in the mid-1800s to warn ships away from the treacherous coral heads below, the iron-pile tower still stands sentinel over a turquoise expanse where sailboats glide and frigatebirds wheel overhead. Sailing toward Sand Key Lighthouse aboard the Schooner America 2.0 puts the landmark in its proper context, seen the way mariners have seen it for generations, from the deck of a tall ship under full canvas.

    The Classic Day Sail traces the calm waters off Key West, and on clear days the silhouette of Sand Key Lighthouse becomes the natural turning point of the journey. As the schooner heels gently with the trade winds, you feel the rigging hum and the salt spray cool your face while the lighthouse grows from a thin pencil on the horizon into a striking skeletal tower set against the open Atlantic. The shallows surrounding Sand Key Lighthouse glow in bands of jade and aquamarine, a vivid contrast to the deeper indigo of the Gulf Stream just beyond. Champagne, beer, wine, and soft drinks are poured as you sail, and there is plenty of space to stretch out on deck, lean against the rail, or simply watch the lighthouse drift past in unhurried silence.

    This sail suits couples looking for a romantic afternoon on the water, photographers chasing that quintessential Keys image, history lovers drawn to maritime landmarks, and anyone who prefers wind and sail over engine noise. Families and first-time sailors find the schooner steady and welcoming, while seasoned boaters appreciate the craftsmanship of a true classic yacht. Whether you come for the views, the breeze, or the quiet thrill of approaching Sand Key Lighthouse under sail, this is a Key West experience that lingers long after you step back onto the dock.

    Related locations

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

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    Reference #WRTAEP

    Adult (Adult (Standard))

    $63.56

    Ages 13 and older.

    0

    Child

    $0

    Ages 2 to 12

    0

    Infant

    $0

    Under 2 years of age

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.9
    Excellent
    592 reviews•Google Maps
    574
    9
    4
    3
    2

    Classic Harbor Line delivers what most travelers dream about when visiting Key West: a gorgeous sailing experience with attentive crew, free-flowing drinks, and those famous sunsets everyone talks about. The sunset cruises seem to be the most popular option, and reviewers consistently rave about the whole package. You're not just getting a boat ride—expect fresh appetizers like shrimp cocktail, veggie platters, cheese and crackers, plus brownies for dessert. The crew gets mentioned by name constantly (Janet, Dan, Brad, Rae, Chelsea, Victoria), which tells you something about how memorable they make the experience. People appreciate the local history commentary during the sail, the smooth sailing even for families with young kids, and the genuinely friendly vibe on board. The America 2.0 schooner itself is described as beautiful and well-maintained. That said, there's one cautionary tale worth noting. While the overwhelming majority had flawless experiences, one family reported last-minute cancellations that derailed their plans entirely. It's a single complaint among overwhelmingly positive feedback, but it's the kind of thing that matters when you're coordinating vacation activities. For what it's worth, everyone else found the crew professional, accommodating, and reliable. Whether you're celebrating something special like a wedding or just want a chill evening on the water to destress, this seems to be one of those experiences that genuinely lives up to the hype. The moonlight sails also get love if you want something different from the sunset crowd.

    What people are saying

    Review 1 of 4
    5/5

    Our sunset cruise was perfect !! We had a great time and the crew was amazing !!! Captain Janet ,Chelsea and Dan were so pleasant and on point !! We definitely will do it again next year ! Nothing but good things to say about our sunset cruise !!

    Photo of Sean Beauchamp19

    Sean Beauchamp19

    May 17, 2026

    Review 1 of 1
    5/5

    Our sunset cruise was perfect !! We had a great time and the crew was amazing !!! Captain Janet ,Chelsea and Dan were so pleasant and on point !! We definitely will do it again next year ! Nothing but good things to say about our sunset cruise !!

    Photo of Sean Beauchamp19

    Sean Beauchamp19

    May 17, 2026

    Great for groups

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